Sodium Carbonate → 2-Amino-6-methyl-6-nitroheptanoic acid

HRID 858954Notes

Reaction equation

HRID 858954 reaction equation
[CH3:1][C:2]([N+:14]([O-:16])=[O:15])([CH3:13])[CH2:3][CH2:4][CH2:5][CH:6]1[NH:10]C(=O)N[C:7]1=[O:12].[OH-].[Na+].[OH-].[K+].C(=O)([O-])[O-:22].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[OH-].[Ca+2].[OH-].[OH-].[Ba+2].[OH-]>>[NH2:10][CH:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([N+:14]([O-:16])=[O:15])[CH3:13])[C:7]([OH:12])=[O:22]

Participants

8

Reactant 7

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 6093208Calcium HydroxideHCID 6093286Barium hydroxideHCID 99427025-(4-Methyl-4-nitropentyl)hydantoin2×

Product 1

HCID 219723372-Amino-6-methyl-6-nitroheptanoic acid

Procedure

5-(4-Methyl-4-nitropentyl)hydantoin is hydrolyzed with alkali to give 2-amino-6-methyl-6-nitroheptanoic acid (see JP-A-11-140076). For example, 5-(4-methyl-4-nitropentyl)hydantoin is hydrolyzed in an aqueous solution preferably in the presence of 1–3 equivalents of alkali, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium hydroxide, barium hydroxide and the like, relative to 5-(4-methyl-4-nitropentyl)hydantoin generally at 20–200° C., preferably 100–150° C. The reaction mixture is concentrated to dryness to give 2-amino-6-methyl-6-nitroheptanoic acid. The obtained 2-amino-6-methyl-6-nitroheptanoic acid can be isolated and/or purified by a conventional method, such as crystallization, chromatography and the like, but generally, can be used in the next step without isolation and/or purification.

Workup

  1. customgenerally at 20–200° C.
  2. custompreferably 100–150° C
  3. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-69e3344babe24f62aa870cd75b916878
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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